Literature DB >> 20166688

Computational study of factors controlling the boat and chair transition states of Ireland-Claisen rearrangements.

Seref Gül1, Franziska Schoenebeck, Viktorya Aviyente, K N Houk.   

Abstract

The origins of the boat transition state preference in the Ireland-Claisen rearrangements studied experimentally by Kishi and co-workers have been explored computationally with Density Functional Theory. Steric interactions in the chair transition states were identified as the principal reason for the boat transition state preference.

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Year:  2010        PMID： 20166688      PMCID： PMC2837782          DOI： 10.1021/jo100033d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: a theoretical study.

Authors:  Mahmood M Khaledy; Mohammad Y S Kalani; Kelli S Khuong; K N Houk; Viktorya Aviyente; Reinhard Neier; Nicolas Soldermann; Joerg Velker
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

Review 2.  Claisen rearrangement over the past nine decades.

Authors:  Ana M Martín Castro
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

3.  Cope reaction families: to be or not to be a biradical.

Authors:  Armando Navarro-Vázquez; Matthias Prall; Peter R Schreiner
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

4.  Gosteli-Claisen rearrangement: substrate synthesis, simple diastereoselectivity, and kinetic studies.

Authors:  Julia Rehbein; Sabine Leick; Martin Hiersemann
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

5.  CASSCF and CASPT2 calculations on the cleavage and ring inversion of bicyclo[2.2.0]hexane find that these reactions involve formation of a common twist-boat diradical intermediate.

Authors:  D A Hrovat; W T Borden
Journal:  J Am Chem Soc       Date:  2001-05-02       Impact factor: 15.419

6.  Gosteli-Claisen rearrangement: DFT study of substituent-rate effects.

Authors:  Julia Rehbein; Martin Hiersemann
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

7.  Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement.

Authors:  Chi-Li Chen; Kosuke Namba; Yoshito Kishi
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

8.  Improved reaction and activation energies of [4+2] cycloadditions, [3,3] sigmatropic rearrangements and electrocyclizations with the spin-component-scaled MP2 method.

Authors:  T P M Goumans; Andreas W Ehlers; Koop Lammertsma; Ernst-Ulrich Würthwein; Stefan Grimme
Journal:  Chemistry       Date:  2004-12-03       Impact factor: 5.236
  8 in total
  5 in total

1.  Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

Authors:  Adam T Hoye; Peter Wipf
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

2.  Combining a Clostridial enzyme exhibiting unusual active site plasticity with a remarkably facile sigmatropic rearrangement: rapid, stereocontrolled entry into densely functionalized fluorinated phosphonates for chemical biology.

Authors:  Kaushik Panigrahi; Gregory A Applegate; Guillaume Malik; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2015-03-05       Impact factor: 15.419

3.  Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

Authors:  Hosea M Nelson; Jonny R Gordon; Scott C Virgil; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-16       Impact factor: 15.336

4.  A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.

Authors:  Eirik Lyngvi; Jeffrey W Bode; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2012-03-01       Impact factor: 9.825

5.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419
  5 in total

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